Benzimidazolinone

Benzimidazolinone
Names
	IUPAC name 2-Benzimidazolinone
	Other names 1,3-Dihydro-2H-benzimidazol-2-one; 2-Hydroxybenzimidazole; N,N′-(1,2-Phenylene)urea
Identifiers
CAS Number	615-16-7 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL2152713;
ChemSpider	11490;
ECHA InfoCard	100.009.467
EC Number	210-412-4;
PubChem CID	11985;
UNII	CV8118UZEW;
CompTox Dashboard (EPA)	DTXSID0060642 ;
	InChI InChI=1S/C7H6N2O/c10-7-8-5-3-1-2-4-6(5)9-7/h1-4H,(H2,8,9,10) Key: SILNNFMWIMZVEQ-UHFFFAOYSA-N;
	SMILES C1=CC=C2C(=C1)NC(=O)N2;
Properties
Chemical formula	C7H6N2O
Molar mass	134.138 g·mol−1
Appearance	white solid
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302
Precautionary statements	P264, P270, P301+P317, P330, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Benzimidazolinone is an organic compound with the formula C₆H₄(NH)₂CO. Also classified as a heterocyclic compound it is a bicyclic urea. It is a tautomer of 2-hydroxybenzimidazole.

Synthesis, structure, applications

Pigment Orange 36

The parent compound is prepared by the carbonylation of 1,2-diaminobenzene. The carbonylation can be effected with carbonyldiimidazole.^[2] Like other ureas, it engages in hydrogen bonding, yielding supramolecular structures. Otherwise, the compound is of little interest.

Substituted 2-benzimidazolinones are commercial dyes and pigments. For example 4-amino-2-benzimidazolinone condenses with diketene to give the acetoacetanilide, which undergoes diazo coupling with various aryldiazonium salts. In this way pigment orange 36 and pigment yellow 154 are produced. These pigments are used in paints and plastics.^[3]

The drug domperidone is a derivative of benzimidazolinone.

References

^ "2-Hydroxybenzimidazole". pubchem.ncbi.nlm.nih.gov.
^ Schwiebert, Kathryn E.; Chin, Donovan N.; MacDonald, John C.; Whitesides, George M. (1996). "Engineering the Solid State with 2-Benzimidazolones". Journal of the American Chemical Society. 118 (17): 4018–4029. doi:10.1021/ja952836l.
^ Jaffe, Edward E. (2004). "Pigments, Organic". Kirk-Othmer Encyclopedia of Chemical Technology. doi:10.1002/0471238961.151807011001060605.a01.pub2. ISBN 978-0-471-48494-3.

[1] "2-Hydroxybenzimidazole". pubchem.ncbi.nlm.nih.gov.

[2] Schwiebert, Kathryn E.; Chin, Donovan N.; MacDonald, John C.; Whitesides, George M. (1996). "Engineering the Solid State with 2-Benzimidazolones". Journal of the American Chemical Society. 118 (17): 4018–4029. doi:10.1021/ja952836l.

[3] Jaffe, Edward E. (2004). "Pigments, Organic". Kirk-Othmer Encyclopedia of Chemical Technology. doi:10.1002/0471238961.151807011001060605.a01.pub2. ISBN 978-0-471-48494-3.

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